(E)-1-[1-(3-Chloro-phen-yl)ethyl-idene]-2-(2,4-dinitro-phen-yl)hydrazine.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(14)H(11)ClN(4)O(4), with the same E conformation about the C=N double bond. The mol-ecules are approximately planar, with a dihedral angle between the benzene rings of 10.24 (12)° in one mol-ecule and 4.73 (12)° in the other. In both mol-ecules, the ortho-nitro groups of the 2,4-dinitro-phenyl units are coplanar to their bound benzene rings, whereas the para-nitro groups are slightly twisted. In each mol-ecule, intra-molecular N-H⋯O hydrogen bonds generate S(6) ring motifs. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into sheets parallel to the (-102) plane. These sheets are stacked by π-π inter-actions, with centroid-centroid distances of 3.7008 (14) and 3.7459 (14) Å. A Cl⋯O short contact [3.111 (2) Å] is observed.

Related literature

For bond-length n class="Chemical">data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2011 ▶); Fun et al. (2011 ▶, 2012 ▶); Nilwanna et al. (2011 ▶). For background to biological activities of hydrazones, see: Angelusiu et al. (2010 ▶); Cui et al. (2010 ▶); Gokce et al. (2009 ▶); Khan et al. (2007 ▶): Loncle et al. (2004 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

C14H11ClN4O4

M = 334.72

Monoclinic,

a = 13.4825 (13) Å

b = 15.1586 (15) Å

c = 16.1281 (12) Å

β = 116.815 (6)°

V = 2941.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.42 × 0.19 × 0.18 mm

Data collection

Bruker APEX DUO CCn class="Chemical">D area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.951

32600 measured reflections

8629 indepenn class="Chemical">dent reflections

4617 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.183

S = 1.01

8629 reflections

417 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); n class="Chemical">data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. n class="Chemical">DOI: 10.1107/S160053681200548X/rz2707sup1.cif

Structure factors: contains datablock(s) I. n class="Chemical">DOI: 10.1107/S160053681200548X/rz2707Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200548X/rz2707Isup3.cml

Adn class="Chemical">ditional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H11ClN4O4	F(000) = 1376
Mr = 334.72	Dx = 1.512 Mg m−3
Monoclinic, P21/c	Melting point = 478–479 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.4825 (13) Å	Cell parameters from 8629 reflections
b = 15.1586 (15) Å	θ = 1.7–30.1°
c = 16.1281 (12) Å	µ = 0.29 mm−1
β = 116.815 (6)°	T = 296 K
V = 2941.8 (5) Å3	Block, orange
Z = 8	0.42 × 0.19 × 0.18 mm

Bruker APEX DUO CCD area-detector diffractometer	8629 independent reflections
Radiation source: sealed tube	4617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 30.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.889, Tmax = 0.951	k = −21→19
32600 measured reflections	l = −22→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0916P)2 + 0.289P] where P = (Fo2 + 2Fc2)/3
8629 reflections	(Δ/σ)max = 0.001
417 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1A	0.83654 (6)	0.45629 (4)	0.39055 (4)	0.0766 (2)
O1A	0.99997 (15)	0.97920 (10)	0.69823 (12)	0.0774 (5)
O2A	1.06555 (14)	0.99861 (10)	0.84524 (12)	0.0711 (5)
O3A	1.2204 (2)	0.76410 (15)	1.05861 (12)	0.1103 (8)
O4A	1.18161 (18)	0.63048 (13)	1.01190 (12)	0.0949 (6)
N1A	0.97877 (14)	0.82236 (11)	0.62719 (11)	0.0553 (4)
H1NA	0.9589	0.8744	0.6200	0.066*
N2A	0.94483 (14)	0.76046 (11)	0.55856 (11)	0.0536 (4)
N3A	1.03978 (14)	0.95052 (11)	0.77797 (13)	0.0545 (4)
N4A	1.18006 (17)	0.70917 (15)	0.99701 (13)	0.0688 (5)
C1A	1.02714 (15)	0.79618 (12)	0.71746 (13)	0.0457 (4)
C2A	1.05891 (15)	0.85647 (12)	0.79264 (13)	0.0449 (4)
C3A	1.10886 (15)	0.82829 (13)	0.88368 (13)	0.0481 (4)
H3A	1.1298	0.8685	0.9322	0.058*
C4A	1.12712 (16)	0.73977 (13)	0.90130 (13)	0.0502 (5)
C5A	1.09807 (17)	0.67883 (13)	0.82982 (14)	0.0556 (5)
H5A	1.1124	0.6192	0.8435	0.067*
C6A	1.04898 (18)	0.70614 (12)	0.74032 (14)	0.0533 (5)
H6A	1.0293	0.6647	0.6930	0.064*
C7A	0.90349 (17)	0.78840 (14)	0.47443 (14)	0.0534 (5)
C8A	0.86585 (16)	0.71840 (15)	0.40185 (13)	0.0514 (5)
C9A	0.87083 (16)	0.63003 (14)	0.42698 (13)	0.0525 (5)
H9A	0.8993	0.6143	0.4893	0.063*
C10A	0.83347 (17)	0.56618 (15)	0.35924 (14)	0.0558 (5)
C11A	0.79092 (17)	0.58681 (18)	0.26572 (14)	0.0636 (6)
H11A	0.7651	0.5428	0.2208	0.076*
C12A	0.78777 (18)	0.67358 (19)	0.24109 (15)	0.0678 (6)
H12A	0.7610	0.6885	0.1787	0.081*
C13A	0.82399 (18)	0.73955 (17)	0.30792 (14)	0.0614 (6)
H13A	0.8203	0.7982	0.2900	0.074*
C14A	0.8916 (3)	0.88420 (17)	0.44724 (17)	0.0849 (8)
H14A	0.9563	0.9159	0.4895	0.127*
H14B	0.8270	0.9082	0.4495	0.127*
H14C	0.8839	0.8896	0.3853	0.127*
Cl1B	0.60994 (6)	1.29099 (4)	1.10126 (4)	0.0783 (2)
O1B	0.58475 (15)	0.77573 (10)	0.80697 (11)	0.0683 (4)
O2B	0.51645 (18)	0.75501 (10)	0.66003 (13)	0.0860 (6)
O3B	0.35381 (19)	0.98474 (14)	0.44260 (11)	0.1013 (7)
O4B	0.3250 (2)	1.11127 (14)	0.48825 (13)	0.1090 (8)
N1B	0.58812 (13)	0.93100 (11)	0.87512 (11)	0.0490 (4)
H1NB	0.6001	0.8750	0.8796	0.059*
N2B	0.60588 (13)	0.99163 (11)	0.94310 (10)	0.0474 (4)
N3B	0.53830 (15)	0.80306 (11)	0.72640 (13)	0.0556 (4)
N4B	0.36352 (19)	1.03694 (14)	0.50342 (13)	0.0729 (6)
C1B	0.53726 (15)	0.95592 (12)	0.78481 (12)	0.0432 (4)
C2B	0.51113 (15)	0.89601 (11)	0.71062 (13)	0.0445 (4)
C3B	0.45551 (17)	0.92247 (13)	0.61880 (13)	0.0507 (5)
H3B	0.4394	0.8822	0.5709	0.061*
C4B	0.42477 (17)	1.00861 (13)	0.59995 (13)	0.0517 (5)
C5B	0.45036 (18)	1.07026 (13)	0.67045 (14)	0.0564 (5)
H5B	0.4293	1.1289	0.6559	0.068*
C6B	0.50633 (18)	1.04464 (12)	0.76078 (14)	0.0513 (5)
H6B	0.5245	1.0865	0.8076	0.062*
C7B	0.64883 (16)	0.96382 (13)	1.02719 (13)	0.0479 (4)
C8B	0.66519 (15)	1.03272 (14)	1.09812 (13)	0.0475 (4)
C9B	0.63316 (16)	1.11936 (14)	1.07065 (13)	0.0505 (5)
H9B	0.6015	1.1343	1.0080	0.061*
C10B	0.64837 (16)	1.18318 (15)	1.13627 (14)	0.0539 (5)
C11B	0.69611 (17)	1.16370 (17)	1.22983 (14)	0.0589 (5)
H11B	0.7068	1.2075	1.2734	0.071*
C12B	0.72749 (19)	1.07829 (18)	1.25720 (14)	0.0631 (6)
H12B	0.7595	1.0640	1.3200	0.076*
C13B	0.71201 (17)	1.01338 (15)	1.19250 (14)	0.0572 (5)
H13B	0.7332	0.9557	1.2123	0.069*
C14B	0.6820 (2)	0.86989 (15)	1.05689 (15)	0.0722 (7)
H14D	0.6413	0.8311	1.0056	0.108*
H14E	0.6656	0.8557	1.1074	0.108*
H14F	0.7602	0.8629	1.0766	0.108*

	U11	U22	U33	U12	U13	U23
Cl1A	0.0978 (5)	0.0648 (4)	0.0690 (4)	−0.0055 (3)	0.0391 (3)	−0.0079 (3)
O1A	0.1049 (13)	0.0437 (8)	0.0721 (11)	0.0150 (8)	0.0298 (10)	0.0122 (8)
O2A	0.0885 (12)	0.0463 (8)	0.0820 (11)	0.0005 (8)	0.0417 (10)	−0.0156 (8)
O3A	0.159 (2)	0.0944 (15)	0.0468 (10)	−0.0004 (14)	0.0199 (11)	0.0000 (10)
O4A	0.1274 (16)	0.0722 (12)	0.0691 (11)	0.0088 (11)	0.0301 (11)	0.0272 (9)
N1A	0.0674 (11)	0.0427 (9)	0.0489 (9)	0.0047 (8)	0.0200 (8)	0.0013 (7)
N2A	0.0591 (10)	0.0508 (9)	0.0439 (9)	0.0023 (8)	0.0170 (8)	0.0003 (7)
N3A	0.0582 (10)	0.0393 (8)	0.0657 (11)	0.0026 (7)	0.0278 (9)	−0.0008 (8)
N4A	0.0792 (13)	0.0687 (13)	0.0522 (11)	0.0052 (10)	0.0240 (10)	0.0111 (10)
C1A	0.0472 (10)	0.0407 (9)	0.0468 (10)	0.0006 (8)	0.0192 (8)	0.0013 (8)
C2A	0.0481 (10)	0.0346 (9)	0.0529 (10)	0.0007 (7)	0.0236 (8)	−0.0007 (8)
C3A	0.0483 (10)	0.0478 (10)	0.0485 (10)	−0.0041 (8)	0.0223 (8)	−0.0054 (8)
C4A	0.0537 (11)	0.0496 (11)	0.0446 (10)	−0.0004 (9)	0.0199 (9)	0.0039 (8)
C5A	0.0666 (13)	0.0363 (9)	0.0582 (12)	0.0001 (9)	0.0233 (10)	0.0042 (8)
C6A	0.0657 (12)	0.0369 (9)	0.0504 (11)	−0.0002 (8)	0.0199 (9)	−0.0035 (8)
C7A	0.0497 (11)	0.0563 (12)	0.0512 (11)	0.0054 (9)	0.0200 (9)	0.0077 (9)
C8A	0.0441 (10)	0.0649 (13)	0.0442 (10)	0.0063 (9)	0.0192 (8)	0.0061 (9)
C9A	0.0506 (11)	0.0646 (13)	0.0408 (10)	0.0008 (9)	0.0193 (8)	0.0008 (9)
C10A	0.0503 (11)	0.0668 (13)	0.0505 (11)	0.0014 (10)	0.0231 (9)	−0.0014 (10)
C11A	0.0521 (12)	0.0900 (18)	0.0467 (11)	−0.0003 (11)	0.0205 (10)	−0.0109 (11)
C12A	0.0616 (13)	0.0988 (19)	0.0394 (11)	0.0085 (13)	0.0194 (10)	0.0060 (11)
C13A	0.0604 (12)	0.0751 (15)	0.0459 (11)	0.0089 (11)	0.0214 (9)	0.0124 (10)
C14A	0.122 (2)	0.0617 (15)	0.0613 (15)	0.0093 (15)	0.0331 (15)	0.0130 (12)
Cl1B	0.1019 (5)	0.0664 (4)	0.0699 (4)	0.0174 (3)	0.0415 (4)	−0.0006 (3)
O1B	0.0926 (12)	0.0426 (8)	0.0695 (10)	0.0050 (7)	0.0364 (9)	0.0099 (7)
O2B	0.1302 (16)	0.0440 (8)	0.0760 (11)	0.0024 (9)	0.0396 (11)	−0.0144 (8)
O3B	0.159 (2)	0.0877 (14)	0.0431 (9)	0.0147 (13)	0.0329 (11)	0.0020 (9)
O4B	0.162 (2)	0.0778 (13)	0.0645 (11)	0.0374 (14)	0.0311 (12)	0.0214 (10)
N1B	0.0603 (10)	0.0419 (8)	0.0455 (8)	−0.0016 (7)	0.0246 (7)	−0.0001 (7)
N2B	0.0531 (9)	0.0474 (9)	0.0445 (8)	−0.0053 (7)	0.0245 (7)	−0.0007 (7)
N3B	0.0685 (11)	0.0395 (9)	0.0606 (11)	−0.0029 (8)	0.0307 (9)	−0.0032 (8)
N4B	0.0972 (15)	0.0665 (13)	0.0486 (11)	0.0051 (11)	0.0273 (10)	0.0099 (10)
C1B	0.0486 (10)	0.0414 (9)	0.0452 (10)	−0.0051 (7)	0.0260 (8)	0.0002 (7)
C2B	0.0517 (10)	0.0348 (9)	0.0504 (10)	−0.0048 (7)	0.0261 (9)	−0.0017 (7)
C3B	0.0636 (12)	0.0452 (10)	0.0470 (10)	−0.0059 (9)	0.0284 (9)	−0.0049 (8)
C4B	0.0663 (13)	0.0476 (11)	0.0425 (10)	−0.0020 (9)	0.0257 (9)	0.0028 (8)
C5B	0.0775 (14)	0.0387 (10)	0.0562 (12)	0.0016 (9)	0.0331 (11)	0.0065 (9)
C6B	0.0708 (13)	0.0386 (9)	0.0481 (10)	−0.0031 (9)	0.0301 (10)	−0.0033 (8)
C7B	0.0459 (10)	0.0526 (11)	0.0448 (10)	−0.0042 (8)	0.0202 (8)	0.0046 (8)
C8B	0.0440 (10)	0.0578 (12)	0.0419 (10)	−0.0066 (8)	0.0204 (8)	0.0019 (8)
C9B	0.0500 (11)	0.0621 (12)	0.0392 (9)	−0.0009 (9)	0.0200 (8)	0.0025 (9)
C10B	0.0508 (11)	0.0626 (13)	0.0513 (11)	−0.0009 (9)	0.0258 (9)	−0.0022 (9)
C11B	0.0598 (12)	0.0763 (15)	0.0458 (11)	−0.0061 (11)	0.0284 (10)	−0.0090 (10)
C12B	0.0655 (13)	0.0870 (17)	0.0378 (10)	−0.0071 (12)	0.0243 (9)	0.0029 (11)
C13B	0.0603 (12)	0.0664 (13)	0.0451 (10)	−0.0026 (10)	0.0240 (9)	0.0083 (10)
C14B	0.0949 (18)	0.0579 (14)	0.0520 (12)	0.0059 (12)	0.0228 (12)	0.0077 (10)

Cl1A—C10A	1.736 (2)	Cl1B—C10B	1.730 (2)
O1A—N3A	1.228 (2)	O1B—N3B	1.232 (2)
O2A—N3A	1.220 (2)	O2B—N3B	1.216 (2)
O3A—N4A	1.220 (3)	O3B—N4B	1.221 (3)
O4A—N4A	1.215 (3)	O4B—N4B	1.218 (3)
N1A—C1A	1.359 (2)	N1B—C1B	1.354 (2)
N1A—N2A	1.363 (2)	N1B—N2B	1.366 (2)
N1A—H1NA	0.8247	N1B—H1NB	0.8610
N2A—C7A	1.284 (2)	N2B—C7B	1.282 (2)
N3A—C2A	1.449 (2)	N3B—C2B	1.449 (2)
N4A—C4A	1.454 (3)	N4B—C4B	1.460 (3)
C1A—C6A	1.410 (3)	C1B—C6B	1.410 (2)
C1A—C2A	1.421 (3)	C1B—C2B	1.414 (2)
C2A—C3A	1.378 (3)	C2B—C3B	1.384 (3)
C3A—C4A	1.371 (3)	C3B—C4B	1.362 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.389 (3)	C4B—C5B	1.390 (3)
C5A—C6A	1.353 (3)	C5B—C6B	1.361 (3)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.489 (3)	C7B—C8B	1.490 (3)
C7A—C14A	1.505 (3)	C7B—C14B	1.504 (3)
C8A—C9A	1.392 (3)	C8B—C13B	1.391 (3)
C8A—C13A	1.395 (3)	C8B—C9B	1.391 (3)
C9A—C10A	1.374 (3)	C9B—C10B	1.379 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.386 (3)	C10B—C11B	1.379 (3)
C11A—C12A	1.369 (4)	C11B—C12B	1.372 (4)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.388 (3)	C12B—C13B	1.380 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C1A—N1A—N2A	119.48 (16)	C1B—N1B—N2B	119.72 (16)
C1A—N1A—H1NA	113.5	C1B—N1B—H1NB	110.5
N2A—N1A—H1NA	125.2	N2B—N1B—H1NB	129.6
C7A—N2A—N1A	117.24 (18)	C7B—N2B—N1B	117.36 (17)
O2A—N3A—O1A	122.28 (17)	O2B—N3B—O1B	122.21 (18)
O2A—N3A—C2A	118.97 (18)	O2B—N3B—C2B	119.09 (18)
O1A—N3A—C2A	118.74 (17)	O1B—N3B—C2B	118.69 (16)
O4A—N4A—O3A	123.2 (2)	O4B—N4B—O3B	123.8 (2)
O4A—N4A—C4A	118.6 (2)	O4B—N4B—C4B	118.1 (2)
O3A—N4A—C4A	118.2 (2)	O3B—N4B—C4B	118.1 (2)
N1A—C1A—C6A	120.38 (17)	N1B—C1B—C6B	120.37 (17)
N1A—C1A—C2A	122.72 (17)	N1B—C1B—C2B	122.88 (16)
C6A—C1A—C2A	116.90 (17)	C6B—C1B—C2B	116.75 (17)
C3A—C2A—C1A	121.59 (17)	C3B—C2B—C1B	121.82 (17)
C3A—C2A—N3A	116.37 (17)	C3B—C2B—N3B	116.22 (17)
C1A—C2A—N3A	122.03 (17)	C1B—C2B—N3B	121.94 (17)
C4A—C3A—C2A	118.68 (18)	C4B—C3B—C2B	118.70 (18)
C4A—C3A—H3A	120.7	C4B—C3B—H3B	120.6
C2A—C3A—H3A	120.7	C2B—C3B—H3B	120.6
C3A—C4A—C5A	121.47 (18)	C3B—C4B—C5B	121.59 (18)
C3A—C4A—N4A	119.25 (19)	C3B—C4B—N4B	119.28 (18)
C5A—C4A—N4A	119.27 (19)	C5B—C4B—N4B	119.14 (19)
C6A—C5A—C4A	120.08 (18)	C6B—C5B—C4B	119.81 (19)
C6A—C5A—H5A	120.0	C6B—C5B—H5B	120.1
C4A—C5A—H5A	120.0	C4B—C5B—H5B	120.1
C5A—C6A—C1A	121.27 (18)	C5B—C6B—C1B	121.28 (18)
C5A—C6A—H6A	119.4	C5B—C6B—H6B	119.4
C1A—C6A—H6A	119.4	C1B—C6B—H6B	119.4
N2A—C7A—C8A	115.29 (19)	N2B—C7B—C8B	114.92 (18)
N2A—C7A—C14A	124.4 (2)	N2B—C7B—C14B	125.14 (19)
C8A—C7A—C14A	120.33 (19)	C8B—C7B—C14B	119.94 (17)
C9A—C8A—C13A	118.7 (2)	C13B—C8B—C9B	118.04 (19)
C9A—C8A—C7A	120.14 (17)	C13B—C8B—C7B	121.96 (19)
C13A—C8A—C7A	121.2 (2)	C9B—C8B—C7B	120.00 (17)
C10A—C9A—C8A	119.60 (19)	C10B—C9B—C8B	120.03 (18)
C10A—C9A—H9A	120.2	C10B—C9B—H9B	120.0
C8A—C9A—H9A	120.2	C8B—C9B—H9B	120.0
C9A—C10A—C11A	122.0 (2)	C11B—C10B—C9B	121.6 (2)
C9A—C10A—Cl1A	119.52 (16)	C11B—C10B—Cl1B	118.84 (18)
C11A—C10A—Cl1A	118.49 (18)	C9B—C10B—Cl1B	119.55 (16)
C12A—C11A—C10A	118.4 (2)	C12B—C11B—C10B	118.6 (2)
C12A—C11A—H11A	120.8	C12B—C11B—H11B	120.7
C10A—C11A—H11A	120.8	C10B—C11B—H11B	120.7
C11A—C12A—C13A	120.9 (2)	C11B—C12B—C13B	120.7 (2)
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.7
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.7
C12A—C13A—C8A	120.4 (2)	C12B—C13B—C8B	121.1 (2)
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.5
C8A—C13A—H13A	119.8	C8B—C13B—H13B	119.5
C7A—C14A—H14A	109.5	C7B—C14B—H14D	109.5
C7A—C14A—H14B	109.5	C7B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C7A—C14A—H14C	109.5	C7B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C1A—N1A—N2A—C7A	−177.38 (18)	C1B—N1B—N2B—C7B	176.29 (17)
N2A—N1A—C1A—C6A	4.3 (3)	N2B—N1B—C1B—C6B	2.4 (3)
N2A—N1A—C1A—C2A	−176.33 (18)	N2B—N1B—C1B—C2B	−176.75 (17)
N1A—C1A—C2A—C3A	−179.36 (18)	N1B—C1B—C2B—C3B	177.62 (18)
C6A—C1A—C2A—C3A	0.1 (3)	C6B—C1B—C2B—C3B	−1.5 (3)
N1A—C1A—C2A—N3A	1.2 (3)	N1B—C1B—C2B—N3B	−0.6 (3)
C6A—C1A—C2A—N3A	−179.35 (18)	C6B—C1B—C2B—N3B	−179.79 (17)
O2A—N3A—C2A—C3A	−1.9 (3)	O2B—N3B—C2B—C3B	3.6 (3)
O1A—N3A—C2A—C3A	176.84 (18)	O1B—N3B—C2B—C3B	−177.77 (18)
O2A—N3A—C2A—C1A	177.57 (18)	O2B—N3B—C2B—C1B	−178.10 (19)
O1A—N3A—C2A—C1A	−3.7 (3)	O1B—N3B—C2B—C1B	0.6 (3)
C1A—C2A—C3A—C4A	−0.5 (3)	C1B—C2B—C3B—C4B	−0.4 (3)
N3A—C2A—C3A—C4A	178.92 (17)	N3B—C2B—C3B—C4B	177.93 (18)
C2A—C3A—C4A—C5A	1.0 (3)	C2B—C3B—C4B—C5B	1.6 (3)
C2A—C3A—C4A—N4A	179.80 (18)	C2B—C3B—C4B—N4B	−178.42 (19)
O4A—N4A—C4A—C3A	169.6 (2)	O4B—N4B—C4B—C3B	171.1 (2)
O3A—N4A—C4A—C3A	−10.0 (3)	O3B—N4B—C4B—C3B	−8.9 (3)
O4A—N4A—C4A—C5A	−11.5 (3)	O4B—N4B—C4B—C5B	−8.9 (4)
O3A—N4A—C4A—C5A	168.8 (2)	O3B—N4B—C4B—C5B	171.1 (2)
C3A—C4A—C5A—C6A	−1.1 (3)	C3B—C4B—C5B—C6B	−0.8 (3)
N4A—C4A—C5A—C6A	−179.8 (2)	N4B—C4B—C5B—C6B	179.3 (2)
C4A—C5A—C6A—C1A	0.6 (3)	C4B—C5B—C6B—C1B	−1.3 (3)
N1A—C1A—C6A—C5A	179.35 (19)	N1B—C1B—C6B—C5B	−176.77 (19)
C2A—C1A—C6A—C5A	−0.1 (3)	C2B—C1B—C6B—C5B	2.4 (3)
N1A—N2A—C7A—C8A	−179.01 (17)	N1B—N2B—C7B—C8B	−179.42 (15)
N1A—N2A—C7A—C14A	0.8 (3)	N1B—N2B—C7B—C14B	0.5 (3)
N2A—C7A—C8A—C9A	3.7 (3)	N2B—C7B—C8B—C13B	−179.25 (18)
C14A—C7A—C8A—C9A	−176.1 (2)	C14B—C7B—C8B—C13B	0.8 (3)
N2A—C7A—C8A—C13A	−177.09 (19)	N2B—C7B—C8B—C9B	0.8 (3)
C14A—C7A—C8A—C13A	3.1 (3)	C14B—C7B—C8B—C9B	−179.11 (19)
C13A—C8A—C9A—C10A	−0.8 (3)	C13B—C8B—C9B—C10B	0.1 (3)
C7A—C8A—C9A—C10A	178.49 (18)	C7B—C8B—C9B—C10B	−179.94 (18)
C8A—C9A—C10A—C11A	0.3 (3)	C8B—C9B—C10B—C11B	0.7 (3)
C8A—C9A—C10A—Cl1A	−178.40 (15)	C8B—C9B—C10B—Cl1B	179.10 (15)
C9A—C10A—C11A—C12A	0.8 (3)	C9B—C10B—C11B—C12B	−0.9 (3)
Cl1A—C10A—C11A—C12A	179.51 (17)	Cl1B—C10B—C11B—C12B	−179.32 (17)
C10A—C11A—C12A—C13A	−1.4 (3)	C10B—C11B—C12B—C13B	0.3 (3)
C11A—C12A—C13A—C8A	0.9 (3)	C11B—C12B—C13B—C8B	0.5 (3)
C9A—C8A—C13A—C12A	0.2 (3)	C9B—C8B—C13B—C12B	−0.7 (3)
C7A—C8A—C13A—C12A	−179.1 (2)	C7B—C8B—C13B—C12B	179.35 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1A	0.82	1.95	2.598 (2)	135
N1B—H1NB···O1B	0.86	1.86	2.589 (2)	141
C5A—H5A···O1Ai	0.93	2.52	3.251 (3)	136
C5B—H5B···O1Bii	0.93	2.33	3.196 (3)	154
C11A—H11A···O3Biii	0.93	2.55	3.402 (3)	153
C11B—H11B···O3Aiv	0.93	2.58	3.429 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1A	0.82	1.95	2.598 (2)	135
N1B—H1NB⋯O1B	0.86	1.86	2.589 (2)	141
C5A—H5A⋯O1Ai	0.93	2.52	3.251 (3)	136
C5B—H5B⋯O1Bii	0.93	2.33	3.196 (3)	154
C11A—H11A⋯O3Biii	0.93	2.55	3.402 (3)	153
C11B—H11B⋯O3Aiv	0.93	2.58	3.429 (3)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .